This invention relates to novel heterocyclic-substituted quinacridone pigments that are useful for the coloring of plastics and other macromolecular materials, coating compositions and paints, and printing and ink jet inks.
The use of quinacridones as pigments is known. E.g., W. Herbst and K. Hunger, Industrial Organic Pigments, 2nd ed. (New York: VCH Publishers, Inc., 1997), pages 454-474, and S. S. Labana and L. L. Labana, "Quinacridones" in Chemical Review, 67, 1-18 (1967). Ring substitution of quinacridones can produce pigments having different coloristic and physical properties but the substituents of commercially useful pigments are typically alkyl, alkoxy, or halogen groups. E.g., Herbst and Hunger at pages 464-465. Quinacridones having more complex substituents are generally not themselves used as commercial pigments but are instead more commonly used as pigment additives to enhance physical and coloristic properties of other quinacridone pigments. E.g., U.S. Pat. Nos. 5,457,203, 5,453,151, 5,424,429, 5,368,641, 5,334,727, 5,286,863, 5,264,032, 5,137,576, 5,229,515, 5,194,088, 5,145,524, 4,895,949, 4,844,742, 4,541,872, 4,478,968, 4,455,173, 4,439,240, 4,256,507, and 4,310,359. Nevertheless, novel substituted quinacridones having suitably modified coloristic and physical properties would still be desirable. It has now been found that the introduction of certain heterocyclic substituents into quinacridones gives unusual properties, including colors not easily attained with quinacridone.